Ethyl vinyl ether → 8-Acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene

HRID 27651

Reaction equation

HRID 27651 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH:7]([CH3:15])[CH:8]([OH:14])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])(=[O:3])[CH3:2].[CH2:16]([O:18][CH:19]=[CH2:20])[CH3:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CCOCC>[C:1]([O:4][CH2:5][CH2:6][CH:7]([CH3:15])[CH:8]([O:14][CH:16]([O:18][CH2:19][CH3:20])[CH3:17])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8023Ethyl vinyl etherHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 233414518-Acetoxy-2,6-dimethyl-5-hydroxy-2-octene

Product 1

HCID 233414488-Acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 8-acetoxy-2,6-dimethyl-5-hydroxy-2-octene (2.27 g, 10.6 mmole), ethyl vinylether (0.82 g. 11.4 mmole), p-toluenesulfonic acid monohydrate (catalytic amount) and ether (50 ml) is stirred at room temperature for 16 hours. The resulting mixture is treated with ether (150 ml) and washes with 5% sodium bicarbonate solution (2×100 ml). The organic phase is dried (Na2SO4), and evaporated in vacuo to give the crude product. The crude material is further purified by column chromatography on silica gel (25 g, 5% ethyl acetate in hexane) to give 8-acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene as a colorless oil.

Workup

  1. dry with materialThe organic phase is dried (Na2SO4)
  2. customevaporated in vacuo
  3. customto give the crude product
  4. customThe crude material is further purified by column chromatography on silica gel (25 g, 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-49094542a80f4e6a902dcd31a870d2f8
Source dataset
uspto-grants-1980_09
Patent number
US04222937

Linked notes

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